Diisopropylamine → 1-(2-t-Butoxycarbonyl-4-phenylbutyl)cyclopentanecarboxylic acid

HRID 274234Notes

Reaction equation

C(NC(C)C)(C)C.[Li]CCCC.CCCCCC.[CH:19]1([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]1.[C:27]1([CH2:33][CH2:34][C:35](=[CH2:43])[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[C:39]([O:38][C:36]([CH:35]([CH2:34][CH2:33][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:43][C:19]1([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:37])([CH3:40])([CH3:41])[CH3:42]

Participants

Conditions

Temperature: 0 °C

Procedure

To diisopropylamine (5.13 g, 50.9 mmol) in tetrahydrofuran (THF) (20 ml) at -60° C., add n-BuLi hexane solution (20.3 ml of 2.5M, 50.9 mmol). Warm to 0° C., cool again to -60° C. and add cyclopentanecarboxylic acid (2.89 g, 25.4 mmol). Warm to 0° C. for 2.5 hr., cool again and add t-butyl 2-(2-phenylethyl)acrylate (5.90 g, 25.4 mmol) in THF (10 ml). After 2 h., warm to 0° C., quench with 5N HCl, extract with hexane, wash with 1N NaHCO3, and concentrate to a solid. Chromatograph on silica, eluting with hexane-ether-HOAc 60:40:1 to obtain an oil.

Workup

temperaturecool again to -60° C.
temperatureWarm to 0° C. for 2.5 hr
temperature, cool again
temperaturewarm to 0° C.
customquench with 5N HCl
extractionextract with hexane
washwash with 1N NaHCO3
concentrationconcentrate to a solid
washChromatograph on silica, eluting with hexane-ether-HOAc 60:40:1
customto obtain an oil

Sources & evidence

ORD record: ord-ff099279d9d24fdb9a1a8a16ace2b2b3
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05389610

Reaction notes

Loading…